


do boys like they're girls who do girls like they're boys

by TheseusInTheMaze



Category: The Umbrella Academy (TV)
Genre: Crossdressing, Cunnilingus, F/M, Gender Play, Incest, Lipstick & Lip Gloss, Podfic Welcome, Strap-Ons, Vaginal Sex
Language: English
Status: Completed
Published: 2019-09-28
Updated: 2019-09-28
Packaged: 2020-10-30 02:13:27
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 7,182
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20806820
Author URL: https://archiveofourown.org/users/TheseusInTheMaze/pseuds/TheseusInTheMaze
Summary: "C'mon. I can go to the bar with you. It'd be great. We both can.""I'm not taking the two of you to a gay bar on drag night," said Klaus. He pointed at Allison. "Youare going to get swarmed by people asking for your autograph and shit like that, and you," he pointed at Diego, "are going to stand there and glower and generally be a killjoy and scare off any of my chances of having fun.""I can go in disguise," Allison pointed out."I'm not a killjoy," said Diego.





	do boys like they're girls who do girls like they're boys

**Author's Note:**

> Betaed by the ever lovely Electra XT!

"My life is over," Klaus said, dramatically draping himself over the kitchen table with a hand over his forehead like a heroine in a certain class of novel. 

"Why is your life over?" Allison leaned against the kitchen counter, munching a piece of toast. 

Diego frowned down at the blender in front of him. It was possibly older than he was, and he was beginning to worry it would choke on the slices of banana he was carefully dropping into it. It had done that before, and he'd had to turn it off, unplug it, then stick a fork into the bottom to fiddle with the slicing bit and unclog all the mess. 

"I was supposed to go to the bar with Vanya tonight," Klaus said, "but she's got a date with that other violin lady—"

"Vanya has a date?" Allison sounded faintly nonplussed.

"Don't worry," said Diego, and he added another banana slice, thinner than the other ones. "I already checked her out. Barely any criminal record."

"Barely any," said Allison. "That doesn't comfort me."

"We've all got barely any criminal record," Klaus said, flapping a hand.

"Excuse you," said Allison, and she put her own hand on her chest. She drew up, and she looked a bit like an opera singer about to start up on a particularly long aria. "_I_ have no such thing."

"The only reason _you_ have no criminal record is because you used to be a lot less scrupulous about using your rumor powers on people when you were still in your prime law breaking days," said Klaus, lighting up a cigarette. It was somewhat odd to see him stretched out like that, his skirt riding up his thighs. Diego let his eyes brush along the pale skin, contrasting with the dark fabric. He was a bit too tired (and too sore) to get especially horny, but he could file it away for a later date. 

"I resent that implication," Allison said, but then she took another bite of her toast— she clearly didn't have any more argument in her. 

"Regardless," said Klaus, "what was that one bit of criminal record this chick has?"

"Jaywalking," said Diego. He poured a bit more orange juice into the blender, then put the lid on. 

"They give tickets for jaywalking?" Allison sounded surprised. 

"That's not a real crime," Klaus said. "It was created by the automobile companies to try to reframe the fact that they were taking over the roads."

There was an audible pause. 

"What?" Diego glanced over at Klaus, frowning. He was going to have to turn the blender on soon, and he was really hoping it actually cooperated this time. 

"You know how you guys keep telling me to get out of the house more?" Klaus blew a smoke ring. 

"Yeah?" Diego gave in, and turned the blender on. It made a slightly worrying high pitched whine, but otherwise seemed to be behaving itself. He turned his attention to his siblings, who were still talking about... whatever it was that they had been talking about. He'd lost the thread. 

It had been a long night. There had been a mugging, and the lady who was being mugged had thought that Diego had been joining in on the mugging and she had hit him in the head with her handbag. He'd run off to save his dignity, but he was trying to find a way to ask Allison whether it was normal normal for women to keep bricks in their purses, because what the fuck else would be that dense? 

"Well," said Klaus, "the library is free and I bring doughnuts so -"

"Where are you getting the money to get doughnuts," Allison interrupted, speaking over the blender. 

Diego turned the blender off, and he poured the smoothie into a glass, then eyed the leftovers in the reserve of the blender. He shrugged, and took a slug of that, too. 

"Not important," Klaus said. "My _point_ is that all these different groups hold meetings, and a few of 'em will talk your ear off if you stand still long enough."

"I wonder what that's like," Diego said, his voice was dry as old bones. 

"_So_," Klaus said, and he shot Diego a pointed look, "one of them was some kind of... pedestrian's rights advocate."

"Pedestrians have the right of way," Diego protested, and he took a sip of his smoothie.

"That's what I said," Klaus agreed. "But they had a pretty compelling argument. Which is besides the point."

"And what's the point?" Allison took a sip of her coffee. She looked nice, but of course she did. Had she ever looked not nice, since puberty? Her hair was down and around her shoulders, and she was wearing a fitted t-shirt and a pair of relaxed jeans. 

"The point," said Klaus, "is that I was supposed to go out with Vanya, and now she's abandoned me to get some."

"Vanya isn't going to just ‘get some’ with this violinist lady," Diego said. As much as he loved Vanya, he couldn't really imagine his mousy sister ever pursuing anyone enough to get some. He knew she wasn't a virgin— he'd heard various tales of her in compromising positions with their various siblings— but... still. 

"Shows what you know," said Klaus, and he wagged a finger at Diego. "But what am I supposed to _do_ if I can't go out?"

"You could just go by yourself," Allison pointed out.

Klaus propped himself up on his elbows, and he gave her a Look. "You mean I, junkie and addict, should go to a bar all by my lonesome?" 

Diego made a face. He did have a point. 

"So why go to a bar in the first place?" Allison drank more coffee, made a face, and then groped for the coffee pot, and poured herself another cup. 

"Because I want to have fun," Klaus said promptly. 

"You can have fun without going to a bar," Diego argued. "I have fun, and I haven't been to a bar since we got into that whole dust up at the veteran bar."

"Your idea of fun is getting into brawls," said Klaus, then he pointed at Allison. "And don't you start— I can't afford the kind of fun that you have."

"When you put it like that, you make it sound like I'm going on thousand dollar cocaine binges or something," Allison protested.

"I want to go to a bar and have bar fun," said Klaus, and now his voice was edging into a whine. "I want to find someone cute and grind on them and then maybe fuck them in the bathroom—"

"That cannot be sanitary," said Allison. 

"And give a blowjob or maybe eat some pussy someplace illicit," Klaus continued, raising his voice to be heard over Allison's protests.

"You are one depraved individual," Diego said, his tone conversational. Although fucked if that wasn't a pleasant image— Klaus in his club gear on his knees, his face up someone's skirt, or in someone's lap. 

"I do my best," Klaus said. "Only not tonight," he added, and he made a face. 

There was a moment of silence— Diego drank more of his smoothie, Allison took another sip of her coffee. Then she spoke up. "I'll go with you," she said. 

"What?" Klaus looked faintly shocked.

"Sure," said Allison. "Could be fun."

"Allison, baby," said Klaus, "I love you dearly, but I don't think this is your kind of bar."

"I'll go with you," said Diego, on impulse. Maybe the image of Klaus using his mouth on someone else was more compelling than Diego had thought it would be. Or maybe he needed some fun in his life, who knew. 

"This isn't your kind of bar either," said Klaus, "although the sentiment is appreciated."

"What kind of bar do you think is my kind of bar?" Allison's tone was mild, but she was beginning to narrow her eyes the way she always did when she was about to get really mad. 

"Your kind of bar has cocktails that cost more than my entire wardrobe," said Klaus. 

"That's not hard to do when all of your clothes come from the bargain bin at the thrift store," said Allison. 

Klaus made a dismissive hand gesture at her. Diego snorted— it was like being sixteen again, the two of them sniping at each other first thing in the morning. "And what kind of bar do you think is _my_ kind of bar?" Diego took yet another slug of his smoothie, and licked the sweetness off of his lips.

"Dark wood, shitty beer," Klaus said promptly.

"I'm insulted you think I'd drink shitty beer," said Diego. 

"C'mon. I can go to the bar with you. It'd be great. We both can." Allison had gotten an idea on her head, and now she wasn't going to let it go. Of course she wasn't. 

"I'm not taking the two of you to a gay bar on drag night," said Klaus. He pointed at Allison. "_You_ are going to get swarmed by people asking for your autograph and shit like that, and you," he pointed at Diego, "are going to stand there and glower and generally be a killjoy and scare off any of my chances of having fun."

"I can go in disguise," Allison pointed out. 

"I'm not a killjoy," said Diego.

"Keep telling yourself that," Klaus told Diego. "I love you dearly," he said to Allison, "please know that. But wearing a pair of sunglasses and covering your hair isn't gonna cut it."

"It's a bar," said Allison. "It's not like they're going to have spotlights." Then she seemed to light on an idea. "I could dress in drag," she suggested. 

Klaus snorted, looked her up and down. "Have you ever crossdressed before?" 

"Well, no," said Allison. "But I could."

"I could do that too," said Diego. It did sound like it could be fun, and mostly he wanted to prove Klaus wrong. 

It probably said a lot about Diego, that he was willing to go this far just to prove Klaus wrong. 

“You, crossdressing?” Klaus crossed his arms, one eyebrow up. “I’ll believe it when I see it.”

“What’s that supposed to mean?” Diego tried not to bristle too hard at that. 

“It doesn’t mean anything bad, don’t get your panties in a twist,” said Klaus. “Or should I say your lack of panties, in this case?”

Diego rolled his eyes, although he was trying not to smile in spite of himself. That hadn’t been half bad. “I can crossdress,” he told Klaus. “I’d be fuckin’ great at it.”

“Fine,” said Klaus, and he threw his hands up. “Fine. You guys win. You can come with me tonight and make sure I stay out of trouble. But,” he added, and he sat up, making eye contact with each of them in turn, “I expect you both to be goddamn _resplendent_.” He stood up, his skirt swirling around his legs, and he sauntered off. 

Diego watched him go, and then he turned to Allison. “You know,” he said, after a moment, “if I didn’t know better, I’d think that he had planned that all out to get us to come with him.”

“Klaus isn’t that devious,” said Allison. “Is he?” 

Diego shrugged, and he took his glass, beginning to make his way towards his room. “I have no idea,” he said, “but I need to sleep.” 

“I’ll wake you up in time to get ready,” said Allison, and she looked entirely too cheerful. 

* * *

Diego didn’t live at the mansion anymore. He was very clear about that, whenever someone asked, and when they didn’t. He had some of his stuff there, and he slept in his old bed occasionally, but he didn’t live there. He had his boiler room apartment, and that was his. 

But sometimes it was nice to shower in a bathroom that wasn’t a locker room, and to sleep in a room that wasn’t in a basement. He lay on the sheets of his childhood bed, his face in his pillow, and he let sleep begin to fall on him. 

If he were going to crossdress, what would he even wear? The only women he interacted with enough to consider borrowing their clothes were Vanya, Mom, and Allison. Vanya didn’t actually wear feminine clothes, and besides, she was so tiny nothing she had would fit. Mom… no. That was just a no go. 

He’d have to ask Allison later, when he got up. She was bound to have _something_ that fit him. 

* * *

Diego was woken up earlier than he would have liked by knocking on his door. He stumbled out of bed, rubbing his eyes, and he opened the door, glaring out.

Allison elbowed past him, heading straight for his wardrobe. "So I figure I can borrow some of your stuff, and you can wear some of mine," said Allison. "We've got a bit of a height difference and I'm not quite so... built, but I think it won't look too bad."

Diego sat on his bed, rubbing his eyes and trying to get his head in something like order. He had a boner— did it count as morning wood, if it wasn't morning? It was morning as far as his body was concerned, since he'd just woken up. He'd considered these philosophical quandaries before, but it seemed especially pertinent with Allison there, muttering to herself as she pawed through his drawers. 

"Most of this stuff is from when we were kids," said Allison, holding up one of Diego's old Academy shirts.

"Well, yeah," said Diego. "Most of my actual clothes are at home. I just crashed here since they're doing those renovations, remember?" He stretched, his arms over his head and his back arching, and he didn't miss the way Allison's eyes tracked the line of his abs and the broad sweep of his shoulders as he did so. 

"Right," said Allison, then; "I'm going to need to borrow your pants."

"My pants," Diego echoed. 

"I can figure out how to work with this," said Allison, and she was holding up a flannel shirt Diego had bought when he was all of sixteen, "but I don't have any men's pants."

"Can't you borrow some of Klaus's?" Diego let his eyes trace over the curve of Allison's ass, as she bent over to rifle through Diego's second drawer. 

"I'm aiming for a specific look with this outfit," she told Diego. "Klaus doesn't fit that look."

Diego opened his mouth to suggest bothering Luther... and then closed it. Luther's clothing wouldn't fit as anything but a dress. "You'll need to roll the pants up," he said instead.

"I can work with that," said Allison. 

"So I assume this gives you free reign to borrow _your_ clothes," Diego said dryly, then; "my underwear? Really?"

"I want to complete the look," Allison said, and she flashed him a grin that he might have described as "cheeky" if he was the type of person to use that word. 

"Down to the bits that nobody will see," said Diego, his tone dubious. Although the idea of Allison in his boxers made his erection twitch against his thigh. He was going to start dripping pre-come soon, if he wasn't careful. 

"It's all about the authentic experience," said Allison, and her tone was so earnest that she had to be pulling his leg.

He gave her a skeptical look, one eyebrow raised, and he was faintly proud of himself that he was able to pull it off, considering his current state of undress. 

"As if you won't go all out too," said Allison. "I know how you work, Diego."

He shrugged. "What's wrong with throwing on a dress and calling it a day?" He hadn't really considered what dressing in drag would mean, other than possibly having to ask Allison to borrow some clothing. 

"I'm shocked at you, Diego," said Allison. "I've never seen you half ass anything in your life." The late afternoon light from the window was sliding in from between Diego's blinds, and it painted her in strips of gold, like some kind of impressionist painting. 

"I know literally nothing about crossdressing," said Diego. 

"And you still volunteered to do it?" Allison looked surprised. 

"Well, yeah," said Diego. "How hard can it be?" 

Allison was beginning to smile. Diego wasn't sure he liked the look at that smile. "Go take a shower," she said, "and come to my bedroom. We can get you ready."

"Don't look so excited," Diego grumbled, standing up and stretching all over again.

"You're one to talk," Allison said, and her eyes dipped down to where his erection was tenting his boxers. 

"Hey, that is a totally natural process," Diego protested. "Although," he added, and he gave her his best smile, slow and seductive, "if you wanted to help me with that..."

"You are such a pig," she said, but her tone was affectionate. "Go shower, and then we can get started."

"If I didn't know better, I'd think that you'd orchestrated this," said Diego, kicking his boxers off and tossing them into the hamper. His cock slapped against his belly, and Allison's eyes went to it. 

"I've got better things to orchestrate," said Allison, watching as Diego leaned over to pick up his towel.

"Still planning world domination?" He wrapped the towel around his waist. 

"Something like that," she agreed. "Meet me in my room when you're done." And with that, she left the room in a whirlwind of perfume and curly hair. 

"That's not reassuring," Diego called after her. 

* * *

Diego didn't jerk off in the shower. He probably should have— he was still hard, as he scrubbed under his arms, across his chest, up and down his legs. It had finally gone down by the time he had finished washing and shaving, even if the excess energy was still surging through him. He wanted to fuck or fight or run or… something. 

Tonight would be fun. 

There was only a little bit of trepidation churning in his gut as he knocked on the door. 

Allison opened the door, and she looked... well, she looked pretty good. She had tied her hair back, and she hadn't put any makeup on her face. She was wearing his pants with the belt cinched tight, and a tank top. 

"I figured out how I'm going to dress you," Allison announced.

Diego snorted. "Do I get a say in this?" He let her usher him into the bedroom, still dripping water, his hair standing at odd angles from toweling it dry. 

"I know more about this than you do," she told Diego, and she indicated her bed. "Now sit, so I can get you ready."

"I can't even sit at the vanity?" He sat down regardless, his towel sliding open along one side, like the slit in a ballgown. It was, admittedly, an odd comparison to make, but he was in that frame of mind. 

"I want it to be a surprise," said Allison, and she was walking towards him, holding a big case. "C'mon. Let me have my fun."

"I'll let you have all the fun you want," Diego promised, which was not what he'd meant to say. He wasn't even sure what he had meant to say at this point. 

Allison gave him an appraising look, one eyebrow up. Then she smiled at him, and she rubbed her hands together. "This is going to be exciting," she said, and something about the way she was smiling made Diego faintly nervous.

"Just don't make me look dumb," said Diego. "Please," he added as an afterthought.

"I'm not going to make you look dumb," said Allison. "I'm going to make you hot." She opened up the case, and it fanned open. Diego was reminded of a a counterfeiter's art set he'd once seen, full of a million different pens and inks and types of paper.

"You saying I'm not hot already?" Diego didn't even try to be subtle about looking down the front of Allison's tank top when she leaned over him. She was wearing a sports bra, but he could still see her cleavage. He wanted to press his face into it, hold her soft breasts in his hands, feel her hard nipples against his palms.

"You know what I mean," said Allison. She had taken him by the chin, and was tilting his face this way and that. "Thanks for shaving," she added. "It's going to make it a little easier to put the makeup on."

"I figured," Diego said, and he licked his lips. “So are you doing makeup first, or clothes?”

“Clothes,” she said. She stood up again, looking at him critically. "I _think_ I know what I'm going to put you in," she said, "but you may have to try some clothes on first."

"I'm game," he said. 

"And you're willing to do all of this just to show Klaus up?" Allison looked faintly impressed, as she went to her closet to dig around.

"He said I couldn't do it," Diego argued, and he watched her hips move in his pants. This shouldn't have been as hot as it was. He'd never been particularly into seeing someone else wear his clothing before. Admittedly, he'd never had a partner who was willing to wear his clothing like this before— maybe he'd have to ask for it more often. 

Admittedly, Allison and Klaus were the only ones who could wear his clothing without it looking silly. Vanya was too small for it to be anything but a tent on her, and Luther was too big not to stretch everything out beyond belief. 

"Diego," Allison said, and Diego snapped out of his reverie. She was holding a blouse of some kind to him— it had short, puffed sleeves and flowers embroidered around the corner.

"Sorry," said Diego, shaking his head and trying to get his brain back into something like working order. "What?"

"Try this on," she said. "It should fit you. It came in a size too large, and I've been too busy to go about returning it."

"Right," said Diego, and he pulled the shirt up and over his head, then letting the fabric flutter down around his torso. It was lighter and softer than what he usually wore, and the fabric was downright _swishy_. His nipple ring was visible through it, which was... slightly weird, but he could live with that. He was going to a drag show— it wasn't as if he was going to be around people who would be offended by something like a nipple ring. 

"Yeah," said Diego. "I think it works."

"I've got a miniskirt that'll suit you, too," said Allison. “I just need to figure out which panties.”

“Panties,” Diego said. “You want me to wear your underwear?” 

“Klaus steals it all the time,” said Allison, “and you guys are about the same size, dick wise.” She was digging through her dresser drawers. 

“I feel weird that you know that,” said Diego. “I’m not complaining,” he added. “I just feel weird that you can make that comparison.” 

Allison gave an expansive shrug, which somehow managed to look even more expansive from behind. He watched the way the muscles of her back bunched up, bulging under the tank top, and the way her shoulder blades seemed to push together. He wanted to come up behind her, press his face into the soft spot where her neck met her shoulders, grind his dick into her ass. 

"Here we go," Allison said, turning around, and she was holding a pair of plum colored panties. They had lace edging along the legs and along the waist, and they were cut high in the thighs. "Try these on."

"Are you sure they're going to fit me?" Diego stood up anyway, and he let his towel drop. He might have preened at the way Allison's eyes flicked down to his cock, which was getting hard again (damn thing had a mind of its own, even all these years past puberty), but he took the panties and slid them on. Then he frowned. "How do I keep my dick from falling out of these?" 

"Hold on a sec," said Allison, and then she was fiddling with the panties, fiddling with his dick. Whatever she was doing was only making him harder, which wasn't helping things much— she snorted against his cheek. "You're such a pervert." Her soft fingers curled around his shaft, her thumb passing over the head, surrounding it with the soft fabric. She was so warm, and he pressed himself a little closer to her, taking in the familiar scent of her; shampoo, soap, perfume, and the warm scent of her skin. 

"You're the one putting your brother in panties," Diego reminded Allison, but when she stepped back, no part of his cock was sticking out from under the fabric. He was still hard, but it was pressed against his body now, and it was more constricting than he would have thought it would be. 

He liked it more than he thought he would. 

"Well," said Allison, and she stepped back, looking him up and down critically, "you're the one letting your sister put you in panties." She licked her lips, and the way she was looking at him mad his stomach get hotter, his cock trying to twitch in the panties, but not having any luck. 

"I mean," said Diego, "I can't really argue with that logic."

"I'm surprised at you, Diego," said Allison, and she turned around, going to her big wardrobe. "I've never known you to back down from an argument, whether you could win it or not."

"I mean," Diego said, his tone thoughtful, "I _could_ try to make an argument out of it, if you'd really like me to." 

Allison snorted. "I wasn't complaining," she told him over her shoulder, and then she was back to rummaging. As she leaned forward, her tank top rode up in the back. He could see the top of... wait a minute.

"Are you wearing a strap on harness?" He crossed his arms over his chest, but that made the seams of the shirt he was wearing creak a bit, which was worrying, so he brought them back down. 

"Yep," Allison said, and when she turned around, she was holding a dark red skirt on a hanger in her hand. "I thought I'd get into character."

"Get into character," Diego echoed. He'd... well, he was pretty well acquainted with that strap on. It was deep blue, and she fucked ruthlessly, almost mechanically, with it. She'd once made him come so hard that he'd hit himself in the chin, which had been impressive, considering he'd been bent over the bed at the time. 

"Well," said Allison, "I've always found it easier to play a role when I'm getting into it. Versus, y'know, just putting on a costume." She took the skirt off of the hanger and handed it to him. 

"I don't have a character," said Diego, and he unzipped the side of the skirt, then began to carefully pull it over his legs. He had thicker thighs than Allison, but narrower hips. It should have fit, even if some of it would be a tight squeeze. He had to suck his stomach a little bit as he zipped the skirt closed, but by the time he'd gotten it all sorted, it more or less hung straight. 

"You should," said Allison, and she stepped back, looking at him with a thoughtful expression. "Okay. Makeup time."

"Am I going to help make you look all dudely?" Diego let himself be pushed back onto the bed, staring up at Allison. She was wearing a sports bra, and her nipples were hard— he could see them poking through the thin fabric, and he wanted to reach up and grab her tits, press them together and rub his face into her cleavage. 

"It can't be that hard to look dudely," she said, unconcerned. 

"You're wrong there," He said. "The art of dudeness is actually quite complex." He was just letting his mouth run— his eyes darted from her tits in front of his face to her crotch, and he could see the bulge of the strap on. Was this what it looked like, when he had a boner? Admittedly, his cock wasn't as big as her strap on, and he usually wore a cup. 

His mouth probably shouldn't have been watering like it was, but then again, he did like sucking cock. 

"Look up at me," said Allison, and he did so, licking his lips. Allison cupped his cheek, her thumb pressing against the hinge of his jaw. "I'm going to put lipstick on you now."

"I've never worn lipstick before," said Diego, as Allison let go of his cheek to rummage through her makeup box. 

"That is a crying shame," said Allison. "It is going to look _amazing_ on you. You've got the mouth for it, and I've got the skills." She was taking out a black tube of lipstick— when she unscrewed it, he saw that the lipstick was a deep purple. The same shade as the panties. 

"Aren't you modest," Diego said, and he obediently tilted his head in the direction she was indicating. 

"Yep," Allison agreed, as she carefully applied the lipstick to his lips. "You need to use more chapstick."

"I don't use any," Diego said, and then he stopped talking, to make it easier for her to keep applying the lipstick..

"God, this is a good position for you." She finished applying the lipstick, putting the tube down in the case..Her thumb rested on his chin, just under his lower lip, and he took it into his mouth, sucking on it. It would smudge the lipstick, but it was worth it, for the look on her face. 

He liked the slightly shocked look she got on her face, and the way her eyes got wide. He knew the glassy eyed expression meant she was turned on, and her eyes were tracking the curve of his mouth. 

"Fuck," Allison said, and her voice was husky, rough. She rested a hand on top of his hand, and her fingers tightened on his hair.

"I'd really like to suck your cock," said Diego, and he made his own voice husky, looking up at her through his eyelashes. He ran his hands up and down her thighs, and his own pants were faintly rough under the palms of his hands. When he pressed down on her hips, he could feel the outline of the harness. He let go of it, and he moved his hands around, to the waist of her pants, to the belt. 

"That's going to delay our getting ready," said Allison. 

"So does that mean stop?" His fingers hovered over the buckle of her belt.

"I didn't say that." Some of her fingers were tangled into the hair at the top of his head, and the rest were tracing along the shaved sides of his head. Her fingers were very warm, and he could feel her eyes boring into him as he undid the buckle for the belt, then unbuttoned them, then unzipped them. 

It wasn't the first time he'd done gone through these motions, not the first time he'd fished a cock out of a pair of boxers and jerked it in his fist. It was, admittedly, the first time he'd done it with a silicone cock, but he wasn't picky. He liked the way that Allison was staring down at him, liked the heft of the silicone in his hand, liked the way she let out a little breath every time he pressed the base of the dildo against her clit. 

Allison's hand moved to the back of his head, her fingernails digging into the delicate skin on the back of his neck. She was shaking, and her thighs were tense. The pants were falling off of her hips, and he wondered what it would be like if she had just fed her cock out through the fly of her pants. The image of that was enough to make his own cock twitch, still stuck in the panties. 

Diego held her hip in one hand, and he held the cock in the other. He looked up at her face and made a big show of licking his lips, then leaned forward, opening his mouth. He guided the head of the dildo into his mouth, and he sucked on it, hollowing his cheeks out and swirling his tongue along the tip. The silicone was solid on his tongue, stretching his jaw, and he kept eye contact with her as he dipped his head forward, letting it fill up more of his mouth, until he had half the shaft in his mouth. He closed his lips fully around it, and he moved his head up and down, making wet, filthy noises.

"I'm g-g-going to have to fix your lipstick," Allison mumbled. Her knees were trembling, and the pants and boxers were pooled down around her ankles now. She was holding on to him tighter, and her hips were rocking forward. "Fuck, you look so good with a cock in your mouth."

He pulled off of her cock, and he held it in his hand, making a big show of placing wet, sloppy kisses along the shaft of it. She was going to have to wash this thing off, or else get lipstick all over his boxers.

Not that it would be the first time he'd had lipstick all over his boxers.

"You know," Diego said, and he didn't even try to stop the smugness from creeping into his voice, "you aren't the first person to say that."

Allison snorted, and she tugged on his hair. 

He let go of her hip, to slide a finger under the harness. He found the lips of her cunt, her pubic hair pasted down with slick. He took the head of her cock back into his mouth, tracing along the underside of the head with the very tip of his tongue. He swirled the tip of his finger along her clit (awkwardly, with the dildo pressed this close), and swirled his tongue over the head of the dildo. 

"Fuck," Allison gasped, and she pressed her hips forward, the dildo going deeper down his throat.

Diego gasped, almost gagged, then readjusted himself. He began to bob his head again, in earnest this time, and he kept rubbing her clit. He wished that he could have fingered her as well, but not at this angle. He settled for making coy eye contact with her, sucking her cock harder, rubbing her clit. 

"I'm... _fuck_!" Allison’s knees were locking, and she was leaning against him more heavily, her hands moving to his shoulders. 

Diego let her dick slide out of his mouth, the wet head rubbing along his cheek. “This might be a little easier if you were lying down," he said. The lipstick smears on the dildo were particularly vivid, matte patches on the shiny surface. 

"A recumbent blowjob," Allison said, breathless. "How decadent." 

"If you can use three syllable words, I'm clearly not working hard enough," said Diego, and he stood up to give her more room. 

It was more difficult than he thought it would be, moving when he was wearing the skirt. He was hard enough that the head of his cock was poking out from the waistband, no doubt leaving a wet spot on the skirt. 

Allison kicked the pants off, shimmying out of the boxers. She lay on the bed, the strap on pointing towards her chin, and her expression was thoughtful. “Will you be able to eat me out while I’m wearing this?” She wrapped her hand around the base of the cock, and she humped into her hand, fucking her fist like a boy masturbating.

“Probably would be easier if you took it off, yeah,” Diego said, climbing onto the bed. He crawled towards her awkwardly, He’d seen girls do that in outfits like this— it was a bit odd to be on the other end of it, but kind of sexy. He might be willing to try this again sometime. 

“That’s not happening,” Allison said flatly. She was squirming, probably pressing the base of the dildo against her clit, grinding her hips forward. 

“You sure?” Diego lay flat on his belly between her open thighs, and he kissed up one of them. He could smell the musky salt of her arousal through the fabric of her harness, and he mouthed along it, as her thighs began to tense up at his sides. 

“Very,” Allison said, and her voice was fervent enough that he got up on his elbows to make eye contact. There was something significant going on in her expression, which he couldn’t entirely understand. 

“Who am I to argue,” said Diego, and he maneuvered a little more, pushing the crotch of the harness to the side and licking her from her hole to her clit, then back again. He had to keep his thumb hooked into the fabric, which was honestly kind of awkward, and he was nudging his tongue under the base of the dildo. 

“You’re… y-y-y-you’re always one to… t-t-t-to argue. Fuck, Diego.” Allison’s voice went high and breathy as he flickered his tongue along the very tip of her clit, then clumsily tried to seal his lips over it. 

It didn’t work too well, but she was still practically gushing against his face, smearing across his lips, along his chin. Her cunt was going to be all marked up from the lipstick, and her heels were digging into his back now, her knees over his shoulders. He pressed closer, until his nose was pressed into the base of the dildo and his tongue was going inside of her, awkwardly fucking her with his tongue. He ground the dildo into her clit (and against his nose, which was… unpleasant, but livable), as she squirmed and moaned against him. 

She was really into this. Way more into this than he’d expect, honestly— he’d have thought it would be awkward, having the dildo pressing against her like this, but he’d almost never seen her writhe like this. She was getting wetter against his mouth, and then in what seemed like no time at all, she was going stiff against him, and her fingers dug into his hair as she came around his tongue. He ground the dildo harder against her clit, and hopefully she wouldn’t get too sore. She didn’t seem to be complaining, and she shivered when he pulled back.

He’d been grinding his hips against the bed, more for the tease than for any fulfillment, and when he sat up again, he hissed, his cock still trapped in the panties. He squeezed his erection through the thin fabric of the skirt and the equally thin fabric of the panties, and it twitched in his hand. 

“I really want you to fuck me,” Allison said. “With this still on. If it’s possible?” She hooked a finger under the velcro waistband of the harness. 

“It should be possible,” said Diego. “Just might take a bit of maneuvering.”

“Maneuvering,” Allison said, deadpan.

Diego licked his lips. An idea was beginning to percolate in the back of his mind, but he was half afraid that Allison would laugh him out of the room. But then again, she’d dressed him in her clothes, and her orgasm was still wet on his face. So why not take the risk?

“I just need to make sure that I’m wet enough.” Diego pulled the skirt up, pushed the waistband of the panties down, just so that he didn’t have to make eye contact. He didn’t want her to laugh at him. 

He heard her throat click as she swallowed. “Wet enough?” Her voice was very quiet.

“Wet enough,” he echoed, and he scooted closer to her, until he was on his knees between her thighs, and the wet head of his cock was pressed against the slimy fabric at the crotch of her harness. “Can you feel how wet I am?” He pushed the crotch aside once again, pressing the very tip of his cock along the line of her slit. 

“Oh,” said Allison, and her voice cracked. “You’re... “ She shook her head. “I’ve... I’m. I’m so hard. For you. I’m so hard for you.” 

“You are,” Diego said, and his own voice was getting breathless. “You’re so hard. I can feel it sliding into me.” He pressed deeper into her, until the dildo pressed into his belly, and he kissed her, beginning to fuck her in earnest. Something about all of this was just… getting to him, worming up into his head, and maybe he was thinking too much about this, but when he gripped the dildo, he felt her eyes on his hand. 

“God, you feel so tight around my cock,” Allison moaned, right up against his lips. “Your cunt… Diego, your cunt… it…” She was beginning to tremble again, getting tighter around him. 

“Your cock,” he said, and his face was pressed into her neck now, taking in the scent of her hair, her skin. He kissed clumsily along the sweet spot where her neck met her shoulder, and when he pulled back to take it all in, he saw the last bits of the purple lipstick smeared on her skin. Some of it must have stayed on his lips, which was unexpected. 

“What about my cock?” She wriggled against him, and she was beginning to shake harder. “Fuck, Diego, I’m going to come in you, I’m going to come… I’m going…” She came— a succession of fluttering around his cock, and he’d never seen her come that fast. 

“I can feel your come inside of me,” he mumbled, and his lips were pressed against his temple. “It’s dripping, it’s so wet, spreading through me.” 

_Should I say that I’m on the pill or something? I know she is, but would that be too much?_ Some doozy part of his brain was gibbering, and then he was pushing himself as deep as he could go, and the pressure was beginning to break at the base of his spine. He came, his cock pulsing inside of her. He tried not to put all of his weight on her, but stayed inside. The dildo was pushing into his stomach.

“Well,” Allison said after a moment. “I’m glad I did the lipstick first.”

“I cannot believe you just said that,” Diego said, and he pulled out of her to lie down next to her, flat on his stomach. The skirt was riding up, and the elastic waistband of the panties was digging into his balls. 

“Listen,” said Allison, and she propped herself up on her elbows. “If I’d given you the whole face of makeup, I’d have to do _all_ of it.” Her hand groped around, found his hand, and squeezed his fingers. 

He squeezed hers back.

**Author's Note:**

> And with that, I have finished Season of Kink! Woo!


End file.
